Chemistry:Lysergine

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Lysergine, also known as 9,10-didehydro-6,8β-dimethylergoline, is an ergot alkaloid and serotonin receptor agonist of the ergoline family.[1][2][3] It is a minor constituent of ergot.[1]

Pharmacology

Lysergine shows selectivity for activation of the serotonin 5-HT2A receptor over several other closely related serotonin receptors (54-fold over the 5-HT2B receptor, 38-fold over the 5-HT2C receptor, and 127-fold over the 5-HT1A receptor).[2][3] The drug is a partial agonist of the 5-HT2A receptor with moderate intrinsic activity (Emax = 57%).[2][3]

Lysergine activation of serotonin receptors[2][3]
5-HT1A 5-HT2A 5-HT2B 5-HT2C
EC50 Emax EC50 Emax EC50 Emax EC50 Emax
342 ± 23 ND 2.7 ± 1.6 57% 145 ± 54 36% 103 ± 9 42%
Notes: EC50 values are nanomolar (nM) and EC50 values are mean ± SEM.[2][3]

An analogue of lysergine, (+)-13-fluorolysergol, is an even more selective agonist of the 5-HT2A receptor than lysergine (EC50 for 5-HT2B and 5-HT2C of >10,000 nM).[2][3] However, this compound has relatively weak maximal efficacy in activating the receptor (Emax = 17%).[2][3]

See also

References

  1. ↑ 1.0 1.1 "Bioconversions of ergot alkaloids". Adv Biochem Eng Biotechnol 44: 123–144. 1991. PMID 1781317. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chem Rev 124 (1): 124–163. January 2024. doi:10.1021/acs.chemrev.3c00375. PMID 38033123. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 "Synthesis of (+)-Lysergol and Its Analogues To Assess Serotonin Receptor Activity". Org Lett 19 (3): 624–627. February 2017. doi:10.1021/acs.orglett.6b03779. PMID 28106398. 




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